Half Moon Bay in October: plan pumpkin shopping, the festival, and a coastal walk

Agree on the main goal: picking a pumpkin, enjoying a lively street festival, or having a relaxed coastal visit. All three are worthwhile, but combining them on a festival weekend can leave most of the day to traffic and queues.

Confirmed festival dates: October 17–18

The 2026 Half Moon Bay Art & Pumpkin Festival takes place on Main Street on October 17–18, 9 am–5 pm, according to the official directions page. The organizer warns that Highway 92 may become congested around 8 am both days. Allow flexibility for arrival, walking in, and returning home; no route is a guaranteed shortcut.

For pumpkin shopping, choose a confirmed farm day

Find a farm through the official directory, then check the farm’s own page. Confirm 2026 seasonal dates, pumpkin purchasing, parking, and charges for extra attractions. An October listing still labeled 2025, or with mismatched weekdays, does not establish this year’s schedule. Wait for clear information before paying.

• Farm half-day: one farm, a local lunch, and an optional walk on an open coastal path. Keep pumpkins and muddy shoes in the trunk and bring hand-cleaning supplies.
• Festival-focused day: arrive at Main Street, choose two or three priority stalls or performances, then leave time for breaks and the trip home. Use the current program rather than last year’s social posts.
• Split the budget into travel and parking, pumpkins, food, and maze or activity charges. Farm entry, festival entry, and individual attractions are different purchases.

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Check the return journey before going by transit

The organizer links to SamTrans and 511. Check the outbound trip, last return service, festival detours, and walking connections from your actual starting station, especially with children or pumpkins. A regular bus is not a free direct shuttle, and festival stops may change.